During his time with the minor league, the Yankees named him their minor league pitcher of the year. Following this event, Baseball American ranked him as the 49th best prospect in baseball. He also placed third for the American League Rookie of the Year. Pettitte, a three-time All-Star, won five World Series championships with the Yankees. He is known as one of the Core Four players who contributed greatly to the teams dynasty that resulted in five championships. He was a part of seven American League pennant-winning teams and one National League pennant-winning team. He also ranks as MLBs all-time post-season wins leader with 19. Among Yankees pitchers, he ranks first in strikeouts, tied-first in games started and third in wins.
While with the Yankees, he became the first pitcher in MLB history to start and win the three series-clinching playoff games in the same year. Pettitte’s awards throughout his career include a two-time Great Houston Area Major League Player of the Year from the Houston Chapter of the Baseball Writers Association of America, an ALCS Most Valuable Player award, a Warren Spahn Award for being the best left-handed pitcher in baseball, a Good Guy Award from the New York Sports Photographers and a Yankees Mid Season Cy Young Award. He also won the American League Championship Series MVP Award for his part in the teams victory.
- An Afternoon/Evening with Andy Pettitte